Synthesis and characterization of lactose fatty acid ester biosurfactants using free and immobilized lipases in organic solvents

Enayati, Mojtaba; Gong, Yijing; Goddard, Julie M.; Abbaspourrad, Alireza

doi:10.1016/j.foodchem.2018.06.051

Cited by 48 publications

(33 citation statements)

References 30 publications

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“…Finally, although some of the sugar-based esters here presented have already been published for other applications and also as possible antibacterial agents [22][23][24][29][30][31][32][33], a detailed comparative study concerning the properties of a relative large number of both aliphatic and aromatic amphiphilic carbohydrate esters as antimicrobial (Gram-positive, Gram-negative, and fungi) and mostly antibiofilm agents is still lacking.…”

Section: Scheme 3 Reagents and Conditions: (mentioning

confidence: 99%

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

et al. 2019

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A small library of sugar-based (i.e., glucose, mannose and lactose) monoesters containing hydrophobic aliphatic or aromatic tails were synthesized and tested. The antimicrobial activity of the compounds against a target panel of Gram-positive, Gram-negative and fungi was assessed. Based on this preliminary screening, the antibiofilm activity of the most promising molecules was evaluated at different development times of selected food-borne pathogens (E. coli, L. monocytogenes, S. aureus, S. enteritidis). The antibiofilm activity during biofilm formation resulted in the following: mannose C10 > lactose biphenylacetate > glucose C10 > lactose C10. Among them, mannose C10 and lactose biphenylacetate showed an inhibition for E. coli 97% and 92%, respectively. At MICs values, no toxicity was observed on Caco-2 cell line for all the examined compounds. Overall, based on these results, all the sugar-based monoesters showed an interesting profile as safe antimicrobial agents. In particular, mannose C10 and lactose biphenylacetate are the most promising as possible biocompatible and safe preservatives for pharmaceutical and food applications.

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Section: Scheme 3 Reagents and Conditions: (mentioning

confidence: 99%

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

et al. 2019

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“…During sugar ester synthesis, fatty acid vinyl esters are utilized as acyl donors. Since vinyl esters are expensive and result in unstable by-products (vinyl alcohols), Enayati et al [65] replaced them with fatty acids, such as lauric acid and palmitic acid, which yielded high lactose ester synthesis (93%) [65]. This method could be further developed by employing renewable resources with a high content of free fatty acids, such as fatty acid distillates.…”

Section: Bioprocess Development Using Whey Lactosementioning

confidence: 99%

“…For instance, palm fatty acid distillate has been successfully valorized towards polyol ester production using a commercial lipase [61]. Even though lactose esters have been recognized for their superior properties and as attractive substitutes of synthetic surfactants [65,66], only pure lactose has been employed for their production until now [57].…”

Section: Bioprocess Development Using Whey Lactosementioning

confidence: 99%

Cheese Whey Processing: Integrated Biorefinery Concepts and Emerging Food Applications

Lappa

Papadaki

Kachrimanidou

et al. 2019

Foods

157

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Cheese whey constitutes one of the most polluting by-products of the food industry, due to its high organic load. Thus, in order to mitigate the environmental concerns, a large number of valorization approaches have been reported; mainly targeting the recovery of whey proteins and whey lactose from cheese whey for further exploitation as renewable resources. Most studies are predominantly focused on the separate implementation, either of whey protein or lactose, to configure processes that will formulate value-added products. Likewise, approaches for cheese whey valorization, so far, do not exploit the full potential of cheese whey, particularly with respect to food applications. Nonetheless, within the concept of integrated biorefinery design and the transition to circular economy, it is imperative to develop consolidated bioprocesses that will foster a holistic exploitation of cheese whey. Therefore, the aim of this article is to elaborate on the recent advances regarding the conversion of whey to high value-added products, focusing on food applications. Moreover, novel integrated biorefining concepts are proposed, to inaugurate the complete exploitation of cheese whey to formulate novel products with diversified end applications. Within the context of circular economy, it is envisaged that high value-added products will be reintroduced in the food supply chain, thereby enhancing sustainability and creating “zero waste” processes.

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“…They are specially developed in the biological and pharmaceutical fields for their antimicrobial, antioxidant, etc., properties [9,10,11,12,13,14,15]. Monosaccharide esters have usually been isolated from natural products or prepared through enzymatic reaction [16,17,18]. Li et al successfully isolated sucrose fatty acid esters from Astragalus membranaceus , however, the isolation yield was less than 0.01% [16].…”

Section: Introductionmentioning

confidence: 99%

“…Li et al successfully isolated sucrose fatty acid esters from Astragalus membranaceus , however, the isolation yield was less than 0.01% [16]. Enayati et al reported that lactose fatty acid ester can be synthesized using immobilized Candida antarctica on Immobead 150, however, the purification of the product requires solvent extraction and high-performance liquid chromatography [17]. Both isolation and enzymatic process are time-consuming and expensive.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives

et al. 2019

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Microbial infections remains a serious challenge in food industries due to their resistance to some of the well-known antibacterial and antifungal agents. In this work, a novel monomyristoyl ester (fructosyl monomyristate) and two other derivatives (i.e., glucosyl and galactosyl monomyristates) were successfully synthesized from myristic acid and monosaccharides in two-step reactions. First, the myristic acid was converted to myristoyl chloride, and then the myristoyl chloride was reacted with fructose, glucose and galactose separately to produce the corresponding monosaccharide monomyristate derivatives. The structures of the synthesized products were confirmed by Fourier transform infrared (FTIR), proton and carbon nuclear magnetic resonance (1H- and 13C-NMR), and mass spectral (MS) data. The monomyristates esters were obtained in reaction yields of 45.80%–79.49%. The esters were then evaluated for their antimicrobial activity using the disc diffusion test. It was found that the esters exhibited a medium antibacterial activity against gram-positive bacteria; however, they showed a weak antibacterial activity against gram-negative bacteria. Amongst the esters, galactosyl myristate yielded the highest antibacterial activity against Salmonella typhimurium, Staphylococcus aureus and Bacillus subtilis, while glucosyl monomyristate exhibited the highest antibacterial activity only against Escherichia coli. Additionally, all products showed remarkable antifungal activity against Candida albicans. These findings demonstrate that monosaccharide monomyristate derivatives are promising for use as biocompatible antimicrobial agents in the future.

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Synthesis and characterization of lactose fatty acid ester biosurfactants using free and immobilized lipases in organic solvents

Cited by 48 publications

References 30 publications

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Cheese Whey Processing: Integrated Biorefinery Concepts and Emerging Food Applications

Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives

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